


Second Time

by vanessa_cardui



Category: Original Work
Genre: Blackmail, Bondage, F/M, Humiliation, Inexperienced rapist, Oral Pegging, POV Rapist, Pegging, Riding Crops, Teenagers of Ambiguous Age
Language: English
Status: Completed
Published: 2019-07-04
Updated: 2019-07-04
Packaged: 2020-06-09 12:58:15
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Rape/Non-Con
Chapters: 1
Words: 5,562
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19476403
Author URL: https://archiveofourown.org/users/vanessa_cardui/pseuds/vanessa_cardui
Summary: "You can't keep doing this," he said."Can and will, D.D.," she said.  "Unless you want me to send that file to the principal."





	Second Time

**Author's Note:**

  * For [penumbralsock](https://archiveofourown.org/users/penumbralsock/gifts).



The first time hadn't been terrible. It was just that Emily had a million and a half things that she'd wanted to do, and she'd done like . . . five. And those five were pretty great, no question, but she'd been way too eager to get it all done and hadn't thought it all through properly, and. . . .

Well, at least David hadn't gotten the idea that she wasn't going to follow through or something like that, because he was there. She'd set up her cameras and when she checked on her phone, he was there, pacing. If he'd been better at technical sorts of things, maybe he would've faked that somehow, and set her up, but David Dawson didn't know how to network things, or anything like that. He was there, and he probably didn't realize the cameras were there, and he was looking pissy about being there.

Emily fought to keep from running to him. She had to consciously slow down every five steps, because she wanted. . .but she couldn't get there all out of breath and tired, because David was going to put up a fight and she was going to win, and--

She had to slow down again. Calm and measured and dignified and intimidating.

David was waiting in the barn that was just on the edge of where Emily's grandpa's farm had been before they moved out there. The road out was a rutted dirt road, and if there'd been bushes on the sides of the road which weren't blackberry thickets, she'd have gone into one of them and jerked off before she went in to the barn. But there wasn't, and she didn't. . . fuck. She stood there for a few minutes, trembling, trying not to run in, trying not to show . . . anything. David didn't need to see anything until Emily decided to show it to him.

Watching him on her phone, he'd been pacing, and when she came into the barn, he was headed away from her. She got a long look at his back. The tight, dark curls, the pale skin under it, the fraying at the collar of his shirt, the way his butt moved under his jeans.

Then, when he turned to see her, there was how mad he was with her. It made her breath catch.

"You can't keep doing this," he said.

"Can and will, D.D.," she said. "Unless you want me to send that file to the principal."

David stepped closer to her, trying to look threatening. Emily trembled a little at that, but not in fear. So brave and angry and proud. Like he was going to get whatever he wanted, because he was who he was.

"You don't have anything on me," he said. "I'll fuck you up until--"

"D.D." said Emily, with authority. "We watched that movie together last week, didn't we? Breaking and entry, and it's not a first offense, is it? And then you broke into the school computer system, and--"

"I just put the password in that she had taped on her desk!" he said.

"You broke into a government computer, and you signed a paper that said that you didn't do it. There was a guy from the FBI in Mr. Lanigan's office the other day, so you've lied to a federal officer about computer crime. And if you try any goddamn thing with me, except doing exactly what I tell you, that video is going to become available to the cops. You'll--"

"I'll tell them," he said. He was sixteen, and she was fifteen, but right then he sounded like he was maybe ten. "I'll tell--"

Emily was smiling, he was being so. . . she clenched her hands in her jacket pocket. "You'll tell them everything, D.D.? Really? Because it's not a story that a lot of guys would really want to see in the papers, is it? I mean, obviously, I'll deny it, and say that you threatened me, and that's why I didn't turn it over, until you said you were going to hurt me, and I just couldn't any more. And who are they going to believe? You, D.D.? Kid who was failing out of high school and who'd gotten banned from just about every mall in the area for shoplifting and who almost got busted for weed, or the kid who does well in all her classes and is always respectful to her elders?"

He glared at her, and it made her weak in the knees. Literally, weak in the knees, like she was going to fall down. Emily had always thought that was a figure of speech, but no. "Strip," she said, and if she didn't sound confident, she sounded confident enough that he didn't argue again.

"Strip," she repeated, a little less shakily. "Or I'm going to give up on this, and you're going to go to jail for messing up everyone's records. And maybe the videos of what happened the last time we had this conversation get out, which isn't going to help your reputation in prison, is it?"

"How did you even get that video!" he said, and she could hear the despair in the way he said it. He was going to do what she wanted.

"Because I'm good at studying, and learned all about computers, unlike everyone else involved. Now, come on. Be a good boy, and get undressed."

He was still defiant when he took of his shirt, which was amazing, and then he was less defiant when he was trying to get his shoes off, and that was amazinger, and there was the way his hang lingered near his crotch, like he was trying to hide from her, even though he'd known what had happened last time, and what was going to happen this time, and Emily was going to pass out, she was so flushed. "Over here," she said, gesturing to the bales she'd gotten ready earlier. She'd spent a long time adjusting them to get the height right, and the restraints that she'd bought set up the way she wanted them. But there wasn't a lot of other stuff that she could've meant, and David went unsteadily over to where she was pointing. His cock was sort of half-hard, and she couldn't look away from the way it swayed, from his hips, from his butt.

"Come on," she said. "Up. On your back. That's a boy."

"Oh fuck you," muttered David. "You're not going to do anything."

"I'm going to do one or two things," said Emily. "But you're not going to be fucking me. Still, I'll tell you what. If you're very very good, I'll let you suck on my breast for a little while after I'm done." His cock twitched. "There, see? You love this."

"I don't fucking love this!" he said. Again, he sounded younger than he was, like a kid who'd started using swear-words and was sure he was going to get into trouble for it. "I want to go home. Emily, please, you don't have to do any of this, I'll do whatever you want, and--"

"I want you to give me your hand," said Emily. He didn't, but she grabbed it anyway, and wrapped the cuff around his wrist.

"What! I--"

"Shut up, David," Emily hissed, and he shut up, when she got his other wrist tied up, and he didn't even say anything when she pulled the cuffs around his ankles and got the buckles fastened. Emily was breathing a little hard when she was done.

"There," she said. "Comfy, D.D.?"

"No," he said. He glared up at her, and she could see the tension in his arms, the way his shoulders looked without a shirt, the little muscles on his sides. He was so pretty. "Look, do what you want. It doesn't matter. You don't have to do this; I'm not going anywhere."

"Because I figured that you were going to change your mind once I got started," said Emily. "This way. . ." there were a few bits of straw that had gotten out from under the tarp or something--the barn hadn't been used for like, three years, but the hay still got everywhere. One of the pieces had gotten into David's hair; she plucked it out, patted his hair. "Stay there," she said, and went to get the gym bag she'd hidden in back.

He struggled a little, testing. The rattle of chains made the hairs stand up on the back of Emily's neck. She'd never heard that before, and it was. . . she shook her head. She was going to hold it together, she was going to do this the way she wanted to do it, she wasn't going to lose control because of a pretty neck or some straw in black hair or the way chains chimed like bells when David struggled.

She'd tested things before she'd told David to come out to the barn. First, she'd confirmed that no matter how loud she shouted, they couldn't hear it in the house, or on the road or anything. Since Grandpa had stopped farming, the back acres had turned into the sort of thicket that nothing would even try to get through, and then there was a highway and a state forest. Barn was down in a little hollow, and there were trees and bushes. She'd tested it with recordings and really good amplifiers, and you couldn't hear anything once she was out of the hollow, let alone back at the house.

And she'd worked out how to get all the straps fastened. It'd been easier when David wasn't there, naked and struggling and looking like he was still the goddamn king of the sophomore class, and she was going to be in trouble if she didn't do what he wanted, right away, and . . . the thing about a strap-on dildo was that it had a lot of straps, and she didn't know where they all went, and if they got twisted she had to untwist them in a way that meant undoing the parts that she'd already gotten right. But she got it on, and then she swaggered out, with the gym bag in one hand, and the riding crop in the other.

The way David was set up, he had to crane his neck to see her. When he did see her, he didn't look thrilled about it. "What the fuck is that?"

Emily was smirking, and she knew it, and she couldn't stop smirking. "It's something that's been screwing up my Amazon recommended purchases," she said. "I mean, also helped give me some ideas, but we'll get to that. First, let's get your legs spread nice and wide."

The reason why she'd put the cuffs on first was because she knew that David was going to object once she brought that out. He did, and he had pretty strong legs. Honestly, if he'd spent more time practicing and less time hanging out with assholes and trying to be cool, he'd be on the football team. Maybe she'd push him to. . . not yet. Too fast. His legs were pretty strong, but he was fighting with one leg at a time, and she was strong enough to pull it back and use the cuff and chain that she'd got to pull his thigh back toward his arm. Then the other one.

He wasn't cursing or anything. Just struggling, as hard as he could. It was like he thought he was going to win. The whole time, it was like he thought he was going to win, and that she'd realized that she was a big stupid girl for thinking that she could do what she wanted with David Dawson. Well, maybe she was big and stupid, because she could do what she wanted with David Dawson. First one knee was pulled back, then the other, and then she was standing between his spread-open thighs.

His cock had lost some of its enthusiasm during that struggle. Emily was a little tempted to lean forward and give it a kiss, but no. Not that anyone would stop her or anything, but that wasn't what she'd planned. If she wanted to at some point, she could. Whenever she wanted. But she was going to do this the way she'd planned. She put the riding crop down across David's stomach, and looked through the gym bag. She'd bought lube. If she'd lost it, and had to. . . no, there it was. Lube.

The internet recommended using a lot of lube, more than expected. She'd already put the gloves on, when she put on the strap-on, and it felt a little weird on her hands. And her fingers felt more than a little weird pushing up into David's ass.

He didn't like that at all. He was tensed up hard, even though his legs were up; the way his feet twisted in that leather collar. . . Emily was glad she'd spent a little extra for the red-dyed leather. It just looked so hot, against his skin, the way he was trying to escape, and the way he couldn't escape.

She got a hold of his cock, which was mostly soft. Soft and warm and sensitive. Emily's hand was still slick with lube, and when she started rubbing it against David's soft little cock, it started twitching and growing. "There you go, D.D.," she said. "That's a boy."

He still was trying to stay closed where her finger was pushing up into his ass. But he couldn't, not with the amount of lube she was using. He gave a little gasp when she pushed in, and then he tried to wriggle away from her, but he couldn't, because while the restraints were from Amazon, the chains were from the old farm equipment, and he wasn't going to be snapping through them like a superhero or something.

Okay. Lube up his butt, and then lube on the plug. She had to stop playing with his cock in order to do that, which was too bad. It was so responsive--first it was soft, and then it stiffened and pulsed and grew, moving with every touch. It was pretty, too. Like, it wasn't huge or anything, but it was proportioned right, and the skin was just a little darker than the rest of his skin, and there was the change near the top, from the circumcision, and the head was so silky smooth--even through the gloves, it was like velvet.

"You know," she said, "if you don't loosen up, this is going to hurt more than it has to. Let alone what happens when it's time for me to actually fuck your ass, you know?"

He struggled to look up at her, and he glared at the butt plug. It wasn't even the biggest one that she'd bought! He was going to freak out. . .but that wasn't for this time. He had to work up to that. She wasn't going to rush things and send him to the hospital, where they'd ask all sorts of questions and get her in trouble. Everything was planned out, and if she just stuck to the plan, it would all go fine.

"Okay, breathe in. . ." David breathed out, and she started pushing the butt plug in.

The internet was right about using too much lube. He wasn't letting her in, but it was so slippery it was going in anyway. At least the first part. It widened out as it got deeper, and she was pretty sure that if she pushed too hard, she'd rupture something. She wanted to. She had a vision of pushing it so hard that he started bleeding, and then that blood would make it slick enough to get all the way in, and maybe he'd be crying. Or begging? He hadn't started begging yet.

No. She'd made her choices, and he was her responsibility; she was going to take care of him properly.

It was about halfway in. The widest part was still in her hand. She could hold it there with one hand. the other hand started stroking his cock again. It'd gotten half-soft when she'd been trying to force the plug in, but it stiffened up quickly as she ran her hand along it.

Honestly, Emily had a lot to learn. About penises in general, and David's in particular. That was fine. She had plenty of time. She started experimenting with pressure, squeezing a little, and watching how he responded. Also his balls were really fun. That was something that they hadn't really mentioned in sex ed, or even in internet porn. But they were soft and dangly, and while his breath got shorter and he got a little flushed when she moved her hand on his penis, he was really expressive and squirmy when she squeezed his balls, or ran them between her fingers, or. . .

She'd been trying to get him to stop tensing so that she could push the plug in. Maybe it'd worked. She pushed, and she pushed a little harder, and he didn't even scream when the widest part of the plug vanished up inside his ass.

Emily had done her research. It was one of those sort of t-shaped plugs, so the base wasn't going to slip up inside of him while she was busy. And the part between the widest part and the base was kinda girthy, because the idea was to loosen him up for an ass fucking, not to fill him up. Definitely girthier than anything she'd want up her ass, but that wasn't really what was happening, was it.

"There you go!" she said. "Okay, smile for a picture!"

"I'm going to fucking kill you," said David.

"And then you'll go to prison, and then your ass is going to get fucked a lot harder, with a lot less lube," said Emily.

She picked up the riding crop, swished it, and then slapped David, hitting his left nipple. He hadn't screamed at all when she'd gotten her fingers up his ass, but he yelped at that. It was really cute.

Her hand went back to his cock. It was throbbing in her hand. "I mean, seems like you like that kind of thing, so maybe it's not so much of a threat, but in which case, what's the fuss all about."

"I don't."

He clearly did, but he didn't want to admit it. "'sokay," said Emily. "I mean, takes a little getting used to, enjoying getting fucked. Anyhow. We'll get back to your fun place later."  
She let go of his cock, walked around the bales that she'd chained him to. He was breathing hard, and she could've spent all day watching that. But there were too many other things that she needed to do, and his mouth. . . 

Emily had set him up so that his head was off the end of the bale. And she'd been pretty careful about measuring the heights. He was straining his neck to keep it up, but that wasn't where he wanted him. She walked around so that she was behind him, and clicked her tongue. Then she swished her hips, to slap his cheek with her strap-on. "Lean back and open up, D.D."

He didn't lean back. Emily grabbed him under his chin, pushed his head back. He struggled, but he'd been holding his head up the whole time, and he didn't have anything to brace against, so she was going to win eventually. She jabbed her strap-on at him, and twisted his head to the side, mouth firmly shut.

So she hit his cock with her riding crop. Hard.

She'd seen guys rolling around after getting hit in the crotch with a baseball or whatever, but she'd never been right up close like that. His whole body jumped, and he threw his head back and screamed, so she pushed the strap-on in. "Suck," she said.

He tried to twist away, so she pushed it harder into his mouth, deeper. He made a choking noise, eyes wide. She pulled out before he threw up on her, and he gasped, drool coming out of the sides of his mouth as he coughed. "Open up and suck," she said. "Or I'm going to hit you again. Harder."

She would, too. Maybe she would even if he did suck, because the way he'd jumped when . . . there was a red mark across the middle of his cock, the same shape as the end of the riding crop. It was gorgeous.

He breathed, as she jabbed at him with the strap-on. Then he opened his mouth, and it slid into him.

Emily was wearing the strap-on over her shorts. She'd tried it different ways, and she couldn't get the pressure to line up in a way that did anything for her, and honestly, that wasn't the point. She was fucking David's face, and he was taking it.

The way he was lined up, if he'd relax, it'd slip down his throat. But he couldn't; he kept gagging as she thrust into him, trying to squirm away, his hands opening and closing helplessly, his feet twisting in those cuffs which had been 19.99 for the set and which were worth it. From where she was standing, she could see the way his stomach and chest heaved when he gagged, and when she braced herself by holding his throat, she could feel him struggling to take the strap-on down his throat, feel him trying. . .he kept trying, because when he didn't, she hit him.

His cock and his balls, and the insides of his thighs, and his chest--his nipples weren't as sensitive as he'd hoped, but he still twisted when she hit him. That riding crop hadn't been expensive at all, and it was great. When he was sucking, she let him be, and he was . . .it was a little hard to train David Dawson. There was still contempt when he looked at her, he still tried to act like he could . . .but it didn't matter. He was tied up, and he was reaching for her strap-on with his mouth. He looked better than anyone had ever looked. There was drool on his face, and when she let him stop to breathe and swallow spit, he was gasping and flushed.

His cock had gotten soft, and while rocking her hips like that was a little bit like sex, there wasn't any way that she was getting off like that, and she wasn't trying. It wasn't about sex. It was about showing him what his new place was, and he was learning.

Finally, she decided that he'd had enough of that. She pulled out, all the way out, and watched him choking, sputtering. There were tears at the corners of his eyes. Probably just from the way she'd been hitting his throat. Still, she reached out, wiped them off, and he didn't stop her. He was so pretty like that, so impossibly pretty; Emily felt herself melting, knew that she wasn't . . . that she didn't have the look she had before, the ice.

"There we go," she said. "And now that we know who's boss, let's give you something you'll like a little more."

She'd softened a little, seeing those tears in his eyes, the way he'd been straining to take the dildo down his throat. When he tried, David could be good. He would be.

And yet, there was a definite sway in her hips as she went back around the bale she'd fastened him to. It was something he was going to enjoy more, and she was going to make him, whether or not he was going to enjoy it more.

There was a hitch in David's breath as she pulled out the plug. On the internet, they'd warned that the lube might dry out, and there could be some tearing, but she hadn't let it sit for that long. And while it would've been hot to just use his spit to lube up her strap-on, she knew that was't going to be slick enough, not for his first time. She lubed it up before she took out the plug, and she pushed it in as soon as the plug was out.

The plug wasn't that much skinnier than the strap-on, so there wasn't any reason for David to scream like that.

"Shh," she said. She stroked his cock, her strap-on still deep inside of him. It was still soft, but there was a faint stirring, as she pushed into him, and pushed back against his cock. "I know that guys get really sensitive about this, but when we're done, I'm going to figure out how to make you come just by doing this. Something to look forward to, right?"

He straightened his neck to look at her, and there were still tears at the corners of his eyes, and he was angry, and he. . . next time, she was going to get a gag. One of those red ball gags, with the leather straps. So she'd put a plug in his ass when she wasn't fucking it, and a gag in his mouth when she wasn't fucking that, and. . . 

It wasn't really clear from the internet how she could be sure if she was hitting the prostate right. But he was definitely getting harder as she played with his cock. It was so. . . she was moving one hand on the cock, and the other was fondling his balls, and he was making this little squeaky breath out every time the strap-on got all the way inside of him. If she hadn't tied him quite so open, maybe his thighs would be closing on her hips. He wasn't thrusting, exactly--it was almost like he was trying to get away from her thrusts, but that was the same thing, really. There was the slickness of the lube, the way he was sliding against . . . 

Emily let go of his cock, and she couldn't tell if his sigh was disappointment or relief. Like there was a difference, like it mattered. She pulled off the gloves, felt his warmth against her hands, his skin on hers, the stiffness of his cock, the softness of it, the smoothness.

She was going to have him inside her. In her mouth, her pussy, her ass--not this time. She had a plan, and she wasn't going to let the way she felt change her plan. But it felt so good against her hand, and there was the way he was trying not to move with her hands, the way he wasn't able to stop moving with her.

There was plenty of porn out there with guys' orgasms in them. Emily had seen lots of it. According to the internet, some of that was faked, and they used a corn-starch mixture for the come that . . . but this wasn't fake. David didn't want to come. He was trying to hold it back, he was straining hard at the restraints, every muscle tensed, his hands balled up in fists, his toes clenched. He was going to, though. Whether or not he wanted to. He had her strap-on in his ass, and her hands on his cock, one sliding along the shaft, the other feeling the tension in his balls, the folds of his skin, the way he--David strained his neck forward, stared at her. "Emily," he said, and she could hear the strain in his voice. "Please, stop, I can't--"

"No," she said, and she gave her hips a little bit of an extra push on that thrust, her hand a little tighter, pulling down toward her. There was a spurt of come, across his chest, another one up onto his face, across his chin and his cheek and Emily's breath caught; three, four more spurts, the last one just a little dribble down from the tip of his cock.  
She was breathing hard, and she wasn't ready to stop. David was, though. He'd been thrusting in time with her, when he'd come, and she'd watched his hands open as the tension left him. But then he started struggling again, as she kept pumping a his cock. He was twisting, begging, screaming a little. There wasn't any way she could stop when he was like that. His cock was still stiff, but it was like, it was stiff but hollow, and there was some give in it, when she squeezed.

"Please, Emily, please, I can't--"

"You'll be here next week," she said, trying for calm.

He hesitated, and she squeezed down on his softening cock, hard. He screamed, and then, defeated, "Yes."

Emily breathed out, and let go.

He hadn't been crying. The whole time, he hadn't been crying, but he sobbed softly at that, limp and loose in the restraints. Emily went over to where he was set up, smiling fondly down at him. Throat worn out, and ass used, and his cock was. . . she unbuckled her strap-on, let it drop to the floor, and pulled over the chair that she'd set up in advance; it was low enough that she could get David's mouth right next to her chest.

He looked so worn out, though. He was still breathing hard, and the way his chest moved with every breath, rattling the chains and everything, and the sweat, and the tears. . . Emily pulled her breasts out of her top, urgently, awkwardly, and put David's mouth on her breast, as she dipped her hand into her shorts, and started rubbing.

The strap-on hadn't exactly worked for her. But it didn't take her at all long to come, David's mouth soft and insistent, lips and tongue on her breast, moving and sucking on her nipple, not biting at all.

He wasn't tamed, he wasn't beaten. Not really. She looked down on him as she moved against her hand, as she breathed and gasped and tightened up, so hard that she thought she was going to pass out. He was just worn out. When he was feeling better, when he was ready to fight, he was going to fight her again.

She unbuckled the restraints on his wrists and ankles, and he slid down to the floor, dazed. She put her stuff back into the gym bag, got dressed and left. He'd. . . it wouldn't be long before he recovered, and it wouldn't be long after that before he got mad.

Once she got back to her room and locked the door, she checked her cameras. David was getting dressed. He was angry; she could see that in his face, the way he was storming around the barn; he punched one of the beams, which made her bite her lip; if she pushed him too far, if she pushed him at the wrong time. . . her hand was back under the waistband of her shorts. He was going to . . . 

Emily thought about sex a lot, but didn't actually masturbate that often. Usually, after she'd come, she was too sensitive to even try again for a couple of hours. But watching that video, she was thrusting against her hand in about five seconds, eyes closed, thinking about a million things at once. The way he'd looked, the way he'd felt, the way he smelled. . . she scrolled back through the videos she'd taken, found the part when she'd been fucking his ass, and he'd been trying not to respond, and he'd sort of collapsed, tears leaking from the corners of his eyes, as his hips had started to move.

That was the moment, that was. . . Emily groaned, fucking her hand hard, staring at that three-second sequence, over and over, the moment of defeat. He'd been beaten by sex, and yeah, he'd recovered and been angry and punching and. . . she saw it again, and fell apart, coming so hard that she was light-headed afterward, hoping that nobody had come home early, because she'd been way too loud, and now she was done, and boneless, and satisfied, and. . . 

There was still that video there. She watched it, smiling, not able to stop smiling. She'd done it, she'd showed him. . . it'd been perfect.

Her head was a little clearer than it had been, and she could think a little straighter. She went back through the footage, picking out screenshots.

Her dad had always said that threats were for people who didn't want to act. There were things that she didn't want to do, and there were things that she did. There; that was a good one. Strap-on up his ass, cropped enough that people could't tell who it was, or where it was, but showing enough that they'd be tempted to guess. Give David a day or two to get mad, and then spread that anonymously, with a "guess who's into getting their ass pounded" sort of caption. And when he got mad about that, send him a few other screenshots. Let him know that she was going to send out one which gave a few more clues about the mystery guy if he didn't shave his junk before the next time they got together. She wanted to see all of him, and she was going to.

The first time hadn't been terrible, despite what people said about first times. But the second time had definitely been better. And the next time? Next time was going to be great.


End file.
